Red Pepper Soup & Portobello Mushroom Grilled Cheese

A couple of weeks ago we spent an afternoon in Central Park. We wandered through the park, marveled at the beautiful scenery and the (still) falling leaves. We ended up at the Alice and Wonderland sculpture near 74th street, where I used to hang out when I was in high school.
The Alice in Wonderland sculpture always reminds me of a painting my father made for me the year I was born. He is a mathematician so the painting has a geometric angle. The piece has an incredible yellow and black tile floor, doors of all shapes and sizes, plastic keys, the Mad Hatter, the Cheshire Cat and Alice herself. I really love this painting.
Anyway, the sculpture and painting got me thinking about childhood and this post is dedicated to Childhood Classics.  (For another Childhood Classics click this previous post).
Nothing say "childhood classic" like tomato soup and grilled cheese.  Well, this recipe is a twist on that classic-- Roasted Red Pepper Soup and Portobello Mushroom Grilled Cheese on Sourdough Bread.  The recipe was featured on Top Chef, Season 2, when contestants were challenged with "updating a childhood classic for T.G.I. Fridays."  This was the winning entry.  I did not adapt the soup at all - it follows the Top Chef cookbook verbatim. I very, very loosely followed the  recipe for the grilled cheese sandwich.
Roasted Red Pepper Soup (Courtesy of Top Chef: The Cookbook)
3 medium red bell peppers
1/4 cup extra-virgin olive oil
1 medium carrot, diced
1 medium celery rib, diced
1 large red onion, diced
Two 28-ounce cans whole tomatoes in juice
1/2 cup chopped fresh basil leaves, plus more for garnish
1 tablespoon balsamic vinegar
Salt and freshly ground black pepper
1/2 cup heavy cream
Roast the red peppers and coarsely chop.  For suggestions on how to roast peppers, click here.
In a large pot, heat the oil over medium-high heat.  Add the carrots, celery, and onion. Cook until they begin to soften, about 5 minutes.  Add the peppers, tomatoes, basil, vinegar, and salt and pepper to taste. Bring to a simmer, lower the heat, and simmer until the tomatoes begin to break down, 25 to 30 minutes.
Remove from heat, transfer to blender, in batches, and blend until smooth.  I use an immersion blender which simplifies this step significantly.
Return the mixture of the pot (if you used a blender), add cream, and stir until combined.  Serve, garnished with basil. 

Portobello Mushrooms Grilled Cheese
2-3 tablespoons of extra-virgin olive oil
1/2 large red onion, thinly sliced
2 large portobello mushroom caps, thinly sliced
1 tablespoon of balsamic vinegar
Salt and freshly group pepper
1-2 tablespoon of unsalted butter
3 fresh sprig of thyme
1 loaf of sourdough bread (8 slices)
1 cup grated provolone cheese
1 cup grated Monterey Jack cheese
In a medium skillet, combine extra-virgin olive oil and red onion.  Cook until the onion starts to soften, about 5 minutes.  Add thinly sliced portobello mushrooms and cook until they begin to soften.  Add balsamic vinegar, salt and pepper to taste, butter and sprigs of thyme.  Cook on medium-low flame for at least 15 minutes, mixing occasionally.  
Remove the thyme sprigs and turn off the flame.
Cut sourdough bread into 8 slices (or more/less, depending on how thin/thick you like your grilled cheese).  Add some cheese and mushrooms to each sandwich.  Lightly butter a griddle or skillet and cook each sandwich until golden brown and cheese has melted.  You can also use a panini press to get the job done. 
Serves 4.
Now dunk your sandwich in the soup and enjoy memories of childhood!
I added a little bit of mustard when I made left-overs...but not recommended if you serve with the soup.